By Lily Goldberg
Photographs by Tricia McCormack
With its black and white checkered floors, chic bar, elegant guest rooms, and beatnik namesake, Doctor Sax House—a new boutique hotel in Lenox named for a 1959 Jack Kerouac novel—offers a sophisticated stay for guests looking to relax in the Berkshires. But it isn’t just for out-of-towners and honeymooners. Hosting DJ sets, social circles, wine tastings, and more, owners Kelly and Bryan Binder have quickly turned Doctor Sax into a “local salon” that attracts creative and curious Berkshires residents all year round.
“What we really believe in is the stewardship of this area,” said Kelly. “We feel very responsible for adding to it and making it better.”
The Binders—previously residents of New York City and East Hampton, New York—relocated to Great Barrington in May 2024, four years after they set eyes on the property at 35 Walker Street. It was love at first sight. In November 2020, they closed on the historic house, and in 2022, they began to renovate it into the boutique property it is today.
As frequent visitors to the area, the Binders knew that Lenox had “wonderful places to go to dinner,” what they felt the town lacked was a casual space to hang out and chat.
The property where Doctor Sax House now sits has a long history of socializing. The building was originally erected in 1874 as a cottage for a Gilded Age estate, and is perhaps best known for housing the Candlelight Inn, a lively landmark with a strong local following. Since the Candlelight closed in 2004, many longtime Lenox residents have been anxiously awaiting the property’s new life.
“One of the first things we did was invite all of the members of the Lenox Chamber of Commerce into the space,” said Kelly. The experience spurred a “cocktails and conversations” series—the kind of mingling Doctor Sax is all about.
“There’s space where someone could be writing their next book, and then later that day, that same room could have a very lively party atmosphere,” said Bryan.
Since opening in July, the Binders have continued to champion community at Doctor Sax: they’ve partnered with local organizations WAM and the Berkshire International Film Festival, hosted holiday events for Thanksgiving and Christmas Eve, and furnished their rooms with textiles and candles from local businesses. They’ve welcomed travelers from France and friends from down the street. And their hip approach has attracted an intergenerational crowd: at any given hour in the hotel’s cozy lobby lounge, you might see young travelers enjoying a laugh, chic older residents having a drink, or the Binders’ young daughter toddling about.
“I think the Berkshires is honestly on its way to becoming an ageless place,” said Kelly. “It’s more about the attitude and the vibe that you’re showing up with.”
